Cbz-3-Iodo-L-Phenylalanine is a Cbz-protected, L-phenylalanine-derived amino acid bearing an iodine substituent at the 3-position of the aromatic side chain, placing it in the class of halogenated, non-natural aromatic amino acid derivatives used for peptide and labeling chemistry. The molecule contains a carboxylic acid functional group and an amino group masked as a benzyloxycarbonyl (Cbz) carbamate, while the iodinated phenyl ring provides a distinct electron-withdrawing handle for controlled chemical reactivity and downstream conjugation strategies. It is employed as a protected amino acid building block in peptide synthesis and as an intermediate for preparing iodinated phenylalanine analogues used in structure-activity studies, chemical labeling, and analytical method development.
CAT No: CP15108
Cbz-3-Iodo-L-Phenylalanine is a Cbz-protected L-phenylalanine derivative bearing an iodine substituent at the 3-position of the aromatic ring, combining a benzyloxycarbonyl (Cbz) N-protecting group with a stereodefined α-amino acid framework. The molecule contains a chiral center at the α-carbon, a free carboxyl group suitable for peptide coupling after activation, and an aryl iodide that can participate in electrophilic aromatic substitution, cross-coupling, and selective functional group transformations. The aromatic iodide provides a handle for late-stage diversification of phenylalanine side-chain analogs while the Cbz group supports orthogonal protection strategies during stepwise synthesis. The resulting reactivity profile makes the compound a practical chiral amino acid intermediate for constructing iodinated peptide building blocks and downstream aryl-functionalized derivatives.
1. Peptide Synthesis
Cbz-3-Iodo-L-Phenylalanine is used in peptide building block preparation where Cbz protection enables controlled amide bond formation at the α-carboxyl group while maintaining the stereochemistry of the L-amino acid during coupling. The aryl iodide on the side-chain can be retained through standard peptide coupling conditions and later transformed to introduce additional substituents on the aromatic ring of the peptide or peptidomimetic scaffold. The carboxylic acid functionality supports activation-based peptide coupling to generate iodinated sequences that can be used for biochemical probes or structure-activity relationship studies. The Cbz group can be removed under hydrogenolysis-compatible conditions to expose the amine for subsequent elongation or conjugation steps, aligning with common protected amino acid synthesis workflows.
2. Side-Chain Functionalization
Cbz-3-Iodo-L-Phenylalanine is applied in synthetic organic chemistry for aromatic diversification via the aryl iodide, enabling Pd-catalyzed cross-coupling routes such as Suzuki, Sonogashira, or Buchwald-Hartwig to install aryl, alkynyl, or heteroaryl substituents on the phenylalanine side chain. The combination of a chiral, Cbz-protected amino acid core with a reactive iodinated aromatic ring supports stepwise construction of functionalized analogs while preserving the α-stereocenter. The protected amine and carboxyl group allow the molecule to act as a handle for downstream conversion into amide-linked derivatives, including iodinated-to-functionalized side-chain transitions after peptide assembly or scaffold elaboration. The resulting products can serve as intermediates for medicinal chemistry libraries, peptidomimetic analogs, and fine chemical synthesis where controlled aromatic substitution is required.
3. Chemical Biology Probes
Cbz-3-Iodo-L-Phenylalanine is suitable for chemical biology research that relies on incorporating iodinated phenylalanine residues into peptides to generate molecular probes for binding studies, labeling strategies, or analytical tracking. The iodinated aromatic ring can be used as a chemical tag precursor for subsequent derivatization, including conversion to alternative aryl groups or attachment of reporter motifs through cross-coupling chemistry. The Cbz-protected amino acid format supports compatibility with peptide synthesis workflows used to generate defined sequences for mechanistic studies and structure-dependent recognition assays. The stereodefined L-configuration and preserved aromatic functionality help maintain side-chain geometry relevant to peptide-target interactions, enabling downstream probe generation and comparative analog synthesis.
4. Pharmaceutical Intermediate Preparation
Cbz-3-Iodo-L-Phenylalanine is employed as a chiral pharmaceutical intermediate in the manufacturing of iodinated amino acid derivatives and peptide-like intermediates used in process chemistry and fine chemical production. The Cbz-protected amine and carboxylic acid functionality support controlled conversion into activated coupling partners or amide-forming intermediates that can be carried through multistep syntheses. The aromatic iodide provides a late-stage functionalization handle that can be leveraged to adjust electronic and steric properties of phenylalanine-based fragments during SAR-driven process development. The compound's defined stereochemistry and orthogonal protection behavior make it compatible with iterative synthetic routes that require robust handling of chiral amino acid building blocks at scale.
5. Peptidomimetics And SAR Studies
Cbz-3-Iodo-L-Phenylalanine is used in peptidomimetic construction and SAR studies where iodinated aromatic side chains serve as modifiable elements for tuning binding interactions and physicochemical properties. The Cbz-protected amino acid framework supports incorporation into peptide analogs through peptide coupling chemistry, while the aryl iodide enables subsequent diversification to generate a series of structurally related analogs with controlled substitution patterns. The presence of the stereodefined α-amino acid unit helps maintain conformational preferences and side-chain orientation typical of phenylalanine-derived motifs. The resulting iodinated-to-functionalized analogs can be used to build structure-activity relationship panels and to generate downstream intermediates for analytical standards and molecular design programs in applied research and industrial R&D.
3. Emerging applications of nanotechnology for diagnosis and therapy of disease: a review
5. Implications of ligand-receptor binding kinetics on GLP-1R signalling
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More